2 Weeks in Oahu Itinerary: Where to Go & What to Do

Oahu in two weeks: start with the energy of Waikiki, trek through volcanic craters, and relax on the pristine beaches of the North Shore.

Ah, Hawaii—just the name summons visions of deserted beaches, cascading waterfalls, palm trees, rainforested valleys and volcanoes oozing lava. It’s a dream destination, and there’s no better place to kickstart your dream island adventure than Oahu.

It’s chock full of natural goodness and a world away from the mainland, which means it’s a secluded slice of paradise. There’s no shortage of adventures in Oahu, which are what attract the growing millions of visitors each year.

And, seriously, there’s so much to pack into an Oahu itinerary that your only problem will be figuring out what not to do. If you plan on spending two weeks in Hawaii, Oahu is a prime option.

Because it’s so popular, Oahu is the most expensive island to hang on, but there are loads of options when it comes to eating, drinking and accommodation, so you’ll be able to shop around and find the perfect places and pads for your budget.

Plus, public transportation is easy to use, though I recommend hiring a campervan or rental car and making this an Oahu self-drive itinerary. That way you’ll be able to get to some of the island’s lesser-known gems. You can also take your own sweet time.

In fact, take your sweet time all the time—there’s so much to do here that you could easily spend months exploring. But if you’ve only got two weeks in Oahu, then this itinerary will help you check off the best highlights. I’ve peppered it with useful travel tips that will help you make the most out of your adventure.

Days 1-3: Top Things to Do in Waikiki

You probably want to start off your Oahu adventure in Waikiki. It’s the most cosmopolitan part of the island and the perfect place for an intro to Hawaii for your 14 days in Oahu.

International travelers, honeymooners, beach lovers and party animals alike gather in flocks here because Waikiki is home to many of the island’s best-known sites and attractions. Make sure to check these must do’s off your Oahu travel itinerary.

Hit the Diamond Head Trail

The Diamond Head trail on Oahu’s South Shore is the island’s most popular hike. That’s because the 1.5-mile round-trip hike, which summits on top of a volcanic cone, leads you on a merry trail across loose gravel and dirt paths. Then it kicks you in the gut with some steep sets of stairs 560 feet up to the top.

Once you get your breath back, it’ll be taken away again by the jaw-dropping 360-degree views out over Waikiki. You can see it all—towering high rises, the glittering Pacific Ocean and the volcano’s ancient crater that formed 300,000 years ago.

The Diamond Head hike time is between 40 and 60 minutes. It’s considered easy and safe for young hikers, the golden-aged and everyone in between, so there’s no excuse to not get up and give it a go and have a bash at it.

Hike to the Manoa Falls Waterfall

Because the Manoa Falls waterfall is Oahu’s most accessible waterfall, the Manoa Falls trail is a busy one.

Sunrise is arguably the best time of day in Oahu, and if you want this gem all to yourself, I recommend an early morning rise. Nothing spoils a beautiful location like a hundred other tourists.

A 1.6-mile trip up and back, the trail takes you through thick bamboo and dense eucalyptus forests, and across gravel paths and boardwalks before landing in front of Manoa Falls.

The waterfall isn’t the biggest one out there, but it does dramatically cascade down 150 feet into a pool surrounded by ferns and trees.

The sweet-smelling guava trees and wild gingers make the Manoa Falls trail even more enchanting. It’s no wonder the original Jurassic Park movie and the TV series, Lost, shot scenes here.

Surf at Waikiki Beach

This internationally famed, two-mile strip of sparkling white sand is the island’s most famous beach and definitely deserves a visit during your two-week trip to Oahu.

Surfers at Waikiki
Surfs up at Waikiki

Surrounded by fancy, world-class resorts, you’ll never have to wander far from your room in search of the perfect wave. The water here is calm, making it a great spot for beginners to sign up for some surf and paddleboard lessons.

If you’d rather people watch and take in all of the action of Waikiki Beach from afar, wander along the nearby Waikiki Beach Promenade.

Make sure you are on the beach in the evening to witness the gorgeous beach sunset. A Waikiki Beach day deserves a spot on your Hawaii itinerary for Oahu.

Fly Over Oahu in a Robinson R-44 Helicopter

If you’re a baller, or just want to feel like one for a little while, treat yourself to a helicopter ride with Novictor Helicopters. It’s one of the most adventurous things to do in Waikiki.

Marvel at the turquoise water and glistening white sand; zoom past Diamond Head’s ancient crater and zip over to view Waikiki’s skyline.

You’ll all have two-way intercom headsets so you can communicate with your pilot about what you’re seeing, and most tours will offer you professional aerial photography and videography to take home.

Diamond Head Oahu aerial shot
Diamond Head from above

Hike the Pali Notches

This is a trail for the badasses—seasoned hikers and climbers only. The Pali Notches is a hike that consists of two deep, narrow mountain passes. These were carved into its ridge by badass ancient Hawaiian warriors to place cannons here in the 1700s to protect Nu’uanu Valley.

The hike is famed for its difficulty, so you’ll earn full bragging rights for completing it—especially the second notch, which requires a vertical climb down with few sturdy handholds.

This short but highly intense trail that requires you to clamber across narrow ridges sandwiched between sheer cliff drops is exhilarating—or terrifying, depending on your attitude.

Things get real fast, so don’t be an idiot and try this with gusting winds, which can knock you right off the cliff. Equip yourself with a pair of sturdy hiking shoes that’s got lots of grip.

Pali Notches
Staring in awe at Pali Notches.

If you make it past the second notch and onwards to the Chimney, sick views over the blue waters of Kaneohe and its lush greenery will be waiting for you.

For an adrenaline-pumping experience on your two weeks in Oahu, take a hike to the Pali Notches.

Accommodation Options in Waikiki, Oahu

If you’re looking for a place to stay near or in the center of the action in Oahu, mere steps away from the beach and its nightlife, then Waikiki is it. But be warned, a stay in this region of the island doesn’t come cheap.

The property’s rooms are air-conditioned for those sweltering hot summer days and equipped with furnished kitchens so you have the option of saving a few bucks by cooking at home. A reception is held every Monday and guests are encouraged to come mingle with fellow travelers while munching on free appetizers.

Seaside Hawaiian Hostel Waikiki – Best Budget Accommodation

This hostel is a favorite among backpackers who are beach bums by day and party-goers by night, as it’s located in the heart of Waikiki. The property is surrounded by shops and restaurants, so you’re spoiled for choice. Seaside Hawaiian Hostel Waikiki offers free coffee, tea and toast to start your day off with, as well as boogie boards and snorkel gear to take to the beach. They also have cheap surfboards for rent, in case surfing is on your Oahu itinerary.

Aqua Ohia Waikiki – Best Mid-Range Accommodation

Aqua Ohia Waikiki is a casual four-minute walk from the beach, so you’ll never have to go far to bake in the sun

Moana Surfrider – Best Luxury Accommodation

Just steps away from Waikiki Beach is the luxury resort of Moana Surfrider. It has its very own private beach area as well as a freshwater pool. Dine at one of the many onsite restaurants for breakfast, lunch, afternoon tea or dinner, and book yourself in for a spa or custom facial at their Moana Lani Spa.


Day 4: Hanauma Bay: Best Snorkeling in Oahu

For thousands of years, Hanauma Bay was where Hawaiian royalty went to party and fish. This crescent-shaped bay was formed inside a volcanic crater as a result of explosions tens of thousands of years ago. “Hana” means bay, and “uma” means curved.

The volcanic eruptions ultimately formed the crater on the seafloor, and then the ocean eventually filled the circular bay with water and life. That’s why you’ll find some of the best snorkeling in Oahu here in Hanauma Bay, on the southeast coast of the island.

The underwater wonderland is a protected marine life conservation area that boasts colorful coral reefs, turtles and over 400 species of fish, including Hawaii’s state fish the humuhumunukunukuapua‘a! ????

Plus, Hanauma Bay limits visitors to preserve the area, and it focuses its efforts on educating tourists on the natural wildlife of the area.

Hanauma Bay snorkeling is a must on your Oahu itinerary.

Day 5-6: Koko Head: One of the Best Hikes in Oahu

With miles of rugged terrain and entire regions dedicated to dense forests and lush valleys, there’s no shortage of hiking trails in Oahu. There’s something for everyone here.

Whether you’re a novice hiker who is a bit of a couch potato at home, or a seasoned pro looking to pack in as many trails as you can on your two weeks in Oahu, you’re likely to find one on this island that suits your abilities.

There’s a heated debate among locals about which are the best hikes in Oahu. But the Koko Crater Trail tops the list.

The Koko Crater Trail, better known as the Koko Head Stairs, is a natural Stairmaster workout. It’ll test your strength and endurance. The 1,048 steps to the top are actually old railroad ties that were mounted to the side of the volcanic cone. The military in World War II mounted them to haul supplies up and down.

These steps are uneven and almost double the width of a normal stair. This means you’re going to have to work twice as hard to make it to the top. Nevertheless, locals will tell you that the Koko Head trail makes for one of the best hikes in Oahu.

It boasts views of Hanauma Bay, Hawaii Kai and the Makapu’u Lighthouse Trail. By the time you make your way down the Koko Head hiking trail, you’ll be drenched in sweat, and your legs will feel like Jell-O. After this, you best head off to a beach in search of a well-deserved cold beer.

Day 7-8: Hop Around on the Best Beaches in Oahu

It would be totally rude to take a trip to Hawaii without spending copious amounts of time laying on its best beaches. As an island, Oahu is (obviously) blessed with endless miles of coastline, where the waters of the Pacific Ocean meet its soft golden sands.

Dive into your favorite read, hit the waves or just drift into beach bum paradise. You’ll wish you had more than just two days for beach time on your two weeks in Oahu, but there are too many adventures awaiting.

Visit Kailua Beach

Picture turquoise-blue water and powdery white sand. When people ask about the best beaches in Oahu, locals and regular visitors alike always recommend Kailua Beach.

This 2.5-mile stretch on the easterly shores of the island has got beautiful waters for swimming and surfing, and soaring ironwood trees to provide you with some shade.

Downtown Kailua is also an easy five-minutes walk away, so stop by and pick up some plate lunches before hanging out for the afternoon on Kailua Beach.

This spot is especially popular for boogie boarding and kayaking, with a lot of rental shops around. And Kailua Beach is where you’ll find locals barbecuing until sundown.

Check out Lanikai Beach

Fittingly named, “Lanikai” means “heavenly sea” in the Hawaiian language. Its crystal clear, azure waters and gentle waves make this a perfect spot for swimming or showing off your best underwater handstands.

With half a mile of golden sand, Lanikai beach is a favorite for sunrise viewing—so pick a morning to drag yourself out of bed early. You won’t regret it; Lanikai is frequently ranked as one of the best beaches in Oahu—and the world, according to Forbes.

Accommodation Options in Kailua

For absolute relaxation during your 14 days in Oahu, stay within walking distance of the island’s best beaches. All you’ll have to do is wake up to the sounds of the ocean and drag yourself across the street before flopping onto the golden sands for the day.

On the property is a barbecue for you to use, and a terrace on which to enjoy the surrounding views. You can also play tennis on site.

Paradise Palms B&B – Best Mid-Range Accommodation

Situated in Kailua, this 5-star bed and breakfast is just two minutes from the beach. All rooms have a kitchenette, so you can enjoy home-cooked meals on the terrace. If you’re lucky, you’ll even score a room with mountain views.

Kailua Guesthouse – Best Mid-Range Accommodation

A breezy 10-minute walk to the beach, Kailua Guesthouse also offers bicycles for rent if you’d rather ride instead.


Day 9-10: Visit the Real-Life Jurassic Park

With impossibly lush valleys, rugged mountains and spectacular coastlines, it’s easy to see why Hollywood keeps coming back to Oahu to film blockbusters. The island’s stunning natural beauty has set the scene for a number of movies—most notably Jurassic Park.

Other timeless favorites that were made on the island are Jumanji and Godzilla. Budget a couple of days into your Oahu itinerary to explore the natural sets of these major films. Spend some time filming your own mini-recreation of the movie —just because you can!

Wander the Ho’omaluhia Botanical Gardens

Featured in Jurassic World, the Ho’omaluhia Botanical Gardens is a 400-acre rainforest that the US Army Corps of Engineers designed for flood protection. It opened its leafy doors in 1982.

Sitting at the foot of the Koolau mountain range, this collection of tropical trees represents countries from around the world. This includes Malaysia, the Philippines, India and Sri Lanka, giving the gardens an exotic vibe.

Botanical Gardens Oahu

The open green spaces and lake full of ducks, geese and piglets are perfect for biking, camping, hiking and fishing.

An afternoon at the botanical gardens makes for a chill addition to your Oahu road trip itinerary. It’s also a nice break from all the hiking and beach time.

Go ATVing or Ziplining at Kualoa Ranch

The best Oahu itinerary wouldn’t be complete without a visit to Kualoa Ranch. It’s a must-visit during your two weeks in Oahu for a gamut of reasons.

For movie buffs, stepping foot on this ranch will hit you with a wave of nostalgia, from Godzilla to 50 First Dates. You’ll see that fallen tree that was featured in the original 1993 Jurassic Park, when three characters hid under it to flee from racing Gallimimus.

This family-owned, 4000-acre nature reserve aims to educate visitors on environmental conservation, as well as traditional Hawaiian values and respect for the culture through sustainable recreation.

Their idea of educational fun consists of nature walks, horseback riding, jungle expeditions, ATVing and zip lining.

You’ll explore the scenic valleys and remote corners of this working cattle ranch in the coolest of ways.

Power across streams and through the dirt on one and two-hour guided ATV tours, or zip line across the treetops for amazing views of the dense rainforest (think: native flora and fauna) and majestic Koolau Range.

There are seven tandem zip lines on this three-hour tour, ranging in length from 200 feet all the way to 1/4 mile, so as part of your two weeks in Oahu, tag a buddy and race them across Kualoa Ranch.

Don’t Forget!

When you’re traveling, don’t forget travel insurance! It makes sure you’re covered in case of medical emergencies, theft, lost baggage, and more. This is one item you absolutely should not take a trip to Hawaii (or anywhere else, for that matter) without. After all, if you can’t afford travel insurance, you can’t afford to travel.

Day 10-14: Haleʻiwa: Four Days Uncovering North Shore Oahu

It’s time for a complete change of pace on your Oahu itinerary. After the buzzing activity of Waikiki, there are the laid-back communities of North Shore Oahu. They are committed to keeping life mellow, dude.

The North Shore is home to the Seven Mile Miracle. It’s a (strangely enough) seven-mile stretch of sand famous for epic waves and sun-drenched beaches. This is where Hawaii’s surfing magic really happens.

You should also make a stop in the artsy surf town of Haleʻiwa. It sits up along the coast from Waikiki, on the other side of the island.

Budget four days of your two weeks in Oahu to uncover the North Shore.

Drive the Windward Coast from Kailua

Oahu’s Windward Coast is the island’s lushest region. As you leave vibrant Waikiki behind and head northwest along the coast, you trade clusters of high-rises for green valleys and stunning natural beauty.

The hustle and bustle of city life will quickly give way to more laid back and relaxed vibes. It’ll be ideal for the rest of your two weeks in Oahu.

Travel all the way to the North Shore, cruising past the lofty peaks of the Koolau Range. Also, be sure to stop in at Valley of the Temples. There, a replica of a Japanese Buddhist temple stands to celebrate the first Japanese immigrants to Hawaii.

Drive past the Kualoa Ranch and keep your eyes peeled for Chinaman’s Hat. It’s a tiny island of Mokolii just offshore from Kualoa Point.

Take a Surf Lesson

Hardcore surfers love the Oahu North Shore. That’s because of the monster waves that roll in during the wintertime, between November and April.

The giant barreling waves sometimes reach a whopping 30 feet and bring in surfers from around the world. This sets the stage for international surfing competitions from The Vans Triple Crown of Surfing and The Eddie (in memory of surfer and lifeguard Eddie Aikau), to the Da Hui Backdoor Shootout and the Da Hui Pipeline Warriors invitation-only North Shore surf competitions.

Surfer riding the Banzai Pipeline at Sunset Beach
Would you surf here?

In the summertime, the waves are more gentle. Beginners can take surfing lessons without risking embarrassment or injury on the massive rollers. It’s a mint place to learn to surf, away from the crowds of Waikiki.

But surf lessons aren’t just for beginners. There are instructors all along North Shore Oahu who have coached and traveled alongside world-class surfers. If you’re an advanced surfer looking to challenge yourself when you visit Oahu, great. These gurus can provide you with personalized guidance and even work on contest strategies.

Have Some Fun on the Beach

It wouldn’t be a true Hawaiian experience if you didn’t budget time in your itinerary to just laze and play on the beach.

With seven miles of glorious sun and sand, it’s easy to spend days hopping from beach to beach. And there’s a spot to suit all North Shore Oahu activities.

For a laid-back afternoon of Frisbee tossing and swimming, check out Pupukea and Haleʻiwa Beach Parks. If you’re looking to catch some more waves, however, head to Waimea Bay and Ali’i Beach Parks or Pipeline Beach.

If turtle viewing is on your Oahu itinerary, don’t miss out on Turtle Beach. Visitors camp out for the afternoon and watch sea turtles hatch, scurry and rest on the island’s shore.

Dive Cageless with Sharks

Forget everything you’ve ever learned about sharks from watching Jaws for this adventure. As part of your two weeks in Oahu, you’re going shark diving—without the cage.

One Ocean Diving runs Hawaii’s first and only cageless shark diving program. They want to change the way people think about these marine animals. They’re so commonly, wrongly portrayed as terrifying monsters in the movies and media.

You’ll learn about the behavior, physiology and biology on a face-to-face encounter with sharks. One Ocean Diving wants you to dive confidently and fearlessly into the ocean to swim with these majestic creatures.


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Suit up, throw your flippers on and jump into the chill of the deep ocean. Observe the grace and intelligence of dozens of tiger, great white, sandbar and hammerhead sharks in the wild.

Though One Ocean Diving also offers sea turtle snorkel trips, this cageless dive is by far their most popular program. Don’t worry, the company holds a 100 percent safety record.

For a daring change of pace on your time on the island, work shark diving onto your list. Challenge you to not hear the Jaws theme music as you plunge into the water.

Hike the Ehukai Pillbox for Sunset

On your Oahu itinerary, hike through the forest on this short but steep 1.6-mile round-trip trail. It leads to a historic World War II bunker.

Located near the hip town of Haleʻiwa, the trail begins next to Sunset Beach Elementary school. It has been a local favorite for many years.

Ehukai Pillbox
Ehukai Pillbox Hike

At the end of the hike, you’ll reach a pillbox, a concrete guardhouse with windows through which to fire weapons. It’ll be covered in eclectic graffiti on the inside. Stand on top of it to take in the bird’s-eye view of the Oahu North Shore. It’s nothing but blue skies against bluer waters.

Note that a sign warning against trespassing is posted just after the first bunker. If you decide to cross, you chance being hit with a fine, so trespass at your own risk.

From the second bunker, if you do dare to trespass, you’ll spot Sunset and Pipeline Beaches below. Time your hike for sundown and watch the sun descend into the glittering waters. Unless you are keen on a quick, painful descent, bring a headlamp for hiking down after dark.

Watch the Sunset at Sunset Beach

This beach’s long-standing reputation for stunning island sunsets is written in its name. On any given day in the winter months, it’s a top choice for surfers looking to catch a big break.

Just off the beach, the world-renowned Banzai Pipeline is a favorite surf break for pro surfers around the world. In the summer, when waters are calm, the crowds thin out and families and first-time surfers enjoy the clear waters.

This two-mile stretch of fine sand accounts for an all-day beach affair on this Oahu itinerary. It’s a favorite spot to see the sky turn shades of pink and orange at sundown.

Accommodation Options on the North Shore

Budget a few night’s stay in Hale‘iwa to help you check off the list of activities.

This property features an outdoor pool and an onsite restaurant for maximum comfort. You’ll also find a fitness center here. Go to work off all the plate lunches you’ll be undoubtedly eating on your two weeks in Oahu.

Sharks Cove Rentals – Best Budget Accommodation

This property is located smack in the middle of the seven-mile miracle, within easy walking distance to three of the best beaches on North Shore Oahu- Sunset, Pipeline, and Waimea Beaches. It’s right across from Sharks Cove—a popular destination for snorkeling in summer. Their snorkel gear is free to use. And bikes are up for hire if you want to cycle between the beaches.

Courtyard by Marriot – Best Mid-Range Accommodation

If you’re driving along Oahu’s Windward Coast to the North Shore from Kailua, a stay at the Courtyard by Marriott in Laie will break up your journey nicely.

Turtle Bay Resort – Best Luxury Accommodation

Every room at Turtle Bay Resort offers an ocean view. Spend your days here golfing on one of two 18-hole courses, or take a five-minute wander over to the beach. When you’re hungry, visit one of the on-site eateries for some modern Hawaiian fare. Then unwind with a massage or facial at the end of the day.


Summing Up Your Two Weeks in Oahu

A playground for outdoor adventurers, a haven for surf bums and a paradise for beachgoers, Oahu truly offers so much.

The choices for dining, sleeping, and shopping are dizzying. Repeat visitors to the island will find that they uncover something new every time to add to their Oahu itinerary.

The laid-back pace of the island is perfect to explore at your leisure. And you can stop in for longer at all the places that you really vibe with. But if the endless summer is still a thing of dreams, all good. It’s still possible to blitz through the island’s highlights if you only have a few weeks to explore.

For those wanting to experience Oahu as fully as possible, this is the best two-week itinerary for Hawaii. With these travel tips and day plans, you’ll hit the island’s best beaches, hikes and attractions. And go home with an epic tan and even more epic stories.


Oahu Itinerary FAQs

Is there enough to do on Oahu for 2 weeks?

Oahu has plenty to keep you busy for 2 weeks or more.

Is Oahu an expensive vacation?

Staying in Oahu isn’t cheap. You can typically get by spending $1000-$2000 per week.

What is the prettiest beach in Oahu?

Kailua is one of the prettiest beaches on Oahu—it’s one of my personal favorites on the island.

What is the cheapest month to go to Oahu?

September is one of the cheapest months to travel to Oahu.

Is Maui or Oahu cheaper?

Visiting Oahu is generally cheaper than visiting Maui.

About the Author

Jeremy Scott Foster

Jeremy Scott Foster is an adventure-junkie, gear expert and travel photographer based in Southern California. Previously nomadic, he’s been to ~50 countries and loves spending time outdoors. You can usually find him on the trail, on the road, jumping from bridges or hustling on his laptop working to produce the best travel and outdoors content today.
  1. Hey, thank you for this! So informative! Will surely make this as my guide on my upcoming Hawaii trip! Can you email me your expenses, just an estimate of the food and transpo for this trip? TYSM

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